p-Toluenesulfonic acid → HCID 68816904, compound

HRID 730571Notes

Reaction equation

HRID 730571 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([CH2:17][CH:18]=[O:19])[C:11]=2[NH:10][C:9]1=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([CH2:17][CH2:18][OH:19])[C:11]=2[NH:10][C:9]1=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 57834998HCID 57834998, compound

Product 1

HCID 68816904HCID 68816904, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(1-Benzyl-2-oxo-2,3-dihydro-1H-benzoimidazol-4-yl)-acetaldehyde (90 mg, 0.29 mmol) was dissolved in acetone and p-toluene sulfonic acid (10 mg) added. The mixture was stirred for 2 hours and then partitioned between ethyl acetate and water. After washing with saturated sodium bicarbonate, water, and brine, the organic layer was dried over Na2SO4, filtered, and concentrated to afford 1-benzyl-4-(2-hydroxy-ethyl)-1,3-dihydro-benzoimidazol-2-one (80 mg, quant). 1H NMR (CDCl3) δ 3.84 (d, 2H, J=2.1 Hz), 5.06 (s, 2H), 6.80-7.02 (M, 3H), 7.20-7.33 (m, 5H), 9.78 (t, 1H, J=2.0 Hz), 10.7 (br s, 1H). MS: 265 (M−H)−.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washAfter washing with saturated sodium bicarbonate, water, and brine
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-67e505708fc2470ea17458f067010f28
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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